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Many states have adopted programs for pandemic relief, targeting underserved students whose academic outcomes suffered most from emergency cancellations and remote schooling. One Virginia state policy, “ALL In,” granted districts $418.3 million primarily for high dosage tutoring to improve student attendance and literacy. As policy implementers, school leaders are integral in the effective execution of ALL In. However, anecdotal evidence suggests that educational leaders are resistant to ALL In due to its uncertain sustainability. As such, ALL In provides an opportunity to explore the relationship between politics, policymaking, and policy implementation. Our analysis illuminates the intersection of leadership and policy enactment by shedding light on implementation processes, school leader perceptions of role and responsibilities, and gaps between policy intent and execution.